{"id":46891,"date":"2023-08-27T12:15:42","date_gmt":"2023-08-27T06:30:42","guid":{"rendered":"https:\/\/thechemistrynotes.com\/?p=46891"},"modified":"2023-08-27T12:15:45","modified_gmt":"2023-08-27T06:30:45","slug":"dieckmann-condensation-mechanism-application","status":"publish","type":"post","link":"https:\/\/thechemistrynotes.com\/dieckmann-condensation-mechanism-application\/","title":{"rendered":"Dieckmann Condensation: Mechanism, Applications, Limitations"},"content":{"rendered":"\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"1205\" height=\"631\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/Dieckmann-condensation.jpg\" alt=\"Dieckmann condensation\" class=\"wp-image-46895\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/Dieckmann-condensation.jpg 1205w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/Dieckmann-condensation-300x157.jpg 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/Dieckmann-condensation-1024x536.jpg 1024w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/Dieckmann-condensation-768x402.jpg 768w\" sizes=\"(max-width: 1205px) 100vw, 1205px\" \/><\/figure>\n\n\n\n<p>Dieckmann condensation involves the intramolecular condensation of diester in the presence of&nbsp;bases to produce \u00df-keto esters.&nbsp;It is named after the German chemist Walter Dieckmann.<\/p>\n\n\n\n<p>The Dieckmann Condensation is effective for producing 5- or 6-membered cyclic \u00df-keto esters and is typically carried out with sodium alkoxide in an alcoholic solvent. If the product contains an enolizable proton, the yields are high.<\/p>\n\n\n\n<div id=\"ez-toc-container\" class=\"ez-toc-v2_0_65 counter-hierarchy ez-toc-counter ez-toc-custom ez-toc-container-direction\">\n<div class=\"ez-toc-title-container\">\n<p class=\"ez-toc-title \" >Table of Contents<\/p>\n<span class=\"ez-toc-title-toggle\"><a href=\"#\" class=\"ez-toc-pull-right ez-toc-btn ez-toc-btn-xs ez-toc-btn-default ez-toc-toggle\" aria-label=\"Toggle Table of Content\"><span class=\"ez-toc-js-icon-con\"><span class=\"\"><span class=\"eztoc-hide\" style=\"display:none;\">Toggle<\/span><span class=\"ez-toc-icon-toggle-span\"><svg style=\"fill: #0a0a0a;color:#0a0a0a\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" class=\"list-377408\" width=\"20px\" height=\"20px\" viewBox=\"0 0 24 24\" fill=\"none\"><path d=\"M6 6H4v2h2V6zm14 0H8v2h12V6zM4 11h2v2H4v-2zm16 0H8v2h12v-2zM4 16h2v2H4v-2zm16 0H8v2h12v-2z\" fill=\"currentColor\"><\/path><\/svg><svg style=\"fill: #0a0a0a;color:#0a0a0a\" class=\"arrow-unsorted-368013\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" width=\"10px\" height=\"10px\" viewBox=\"0 0 24 24\" version=\"1.2\" baseProfile=\"tiny\"><path d=\"M18.2 9.3l-6.2-6.3-6.2 6.3c-.2.2-.3.4-.3.7s.1.5.3.7c.2.2.4.3.7.3h11c.3 0 .5-.1.7-.3.2-.2.3-.5.3-.7s-.1-.5-.3-.7zM5.8 14.7l6.2 6.3 6.2-6.3c.2-.2.3-.5.3-.7s-.1-.5-.3-.7c-.2-.2-.4-.3-.7-.3h-11c-.3 0-.5.1-.7.3-.2.2-.3.5-.3.7s.1.5.3.7z\"\/><\/svg><\/span><\/span><\/span><\/a><\/span><\/div>\n<nav><ul class='ez-toc-list ez-toc-list-level-1 ' ><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-1\" href=\"https:\/\/thechemistrynotes.com\/dieckmann-condensation-mechanism-application\/#what-is-dieckmann-condensation\" title=\"What is Dieckmann condensation?\">What is Dieckmann condensation?<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-2\" href=\"https:\/\/thechemistrynotes.com\/dieckmann-condensation-mechanism-application\/#mechanism-of-dieckmann-condensation\" title=\"Mechanism of Dieckmann condensation\">Mechanism of Dieckmann condensation<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-3\" href=\"https:\/\/thechemistrynotes.com\/dieckmann-condensation-mechanism-application\/#applications-of-dieckmann-condensation\" title=\"Applications of Dieckmann condensation\">Applications of Dieckmann condensation<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-4\" href=\"https:\/\/thechemistrynotes.com\/dieckmann-condensation-mechanism-application\/#limitations-of-dieckmann-condensation\" title=\"Limitations of Dieckmann condensation\">Limitations of Dieckmann condensation<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-5\" href=\"https:\/\/thechemistrynotes.com\/dieckmann-condensation-mechanism-application\/#-references\" title=\"&nbsp;References\">&nbsp;References<\/a><\/li><\/ul><\/nav><\/div>\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"what-is-dieckmann-condensation\"><\/span><strong>What is Dieckmann condensation?<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>The Dieckmann condensation is an organic reaction that uses an alkoxide base in alcohol to generate a carbon-carbon bond between two\u00a0ester groups. The end outcome is a cyclic \u03b2&#8211;ketoester. Dieckmann condensation is Intramolecular <a href=\"https:\/\/thechemistrynotes.com\/claisen-condensation-reaction-mechanism\/\">Claisen condensation.<\/a> It is an organic process that occurs when an ester of C6, C7, or C8 dibasic acid undergoes intramolecular condensation in the presence of condensing agents such as sodium, sodium ethoxide, or potassium t-butoxide.\u00a0<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"975\" height=\"296\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-166.png\" alt=\"\" class=\"wp-image-46892\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-166.png 975w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-166-300x91.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-166-768x233.png 768w\" sizes=\"(max-width: 975px) 100vw, 975px\" \/><\/figure>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"mechanism-of-dieckmann-condensation\"><\/span><strong>Mechanism of Dieckmann condensation<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>In this mechanism, the base deprotonates the ester at the \u03b1-position, resulting in a generation of carbanion, which subsequently attacks the carbon of the second ester group to produce cyclic enol. The synthesis of the \u03b2-keto ester\u00a0is now caused by protonation.<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"983\" height=\"523\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-167.png\" alt=\"\" class=\"wp-image-46893\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-167.png 983w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-167-300x160.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/08\/image-167-768x409.png 768w\" sizes=\"(max-width: 983px) 100vw, 983px\" \/><\/figure>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"applications-of-dieckmann-condensation\"><\/span><strong>Applications of Dieckmann condensation<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>5-, 6-, 7-, and 8-membered rings are produced in high yields by the Dieckmann condensation.<\/li>\n\n\n\n<li>Because of the steric stability of five- and six-membered rings, these structures will develop preferentially.<\/li>\n\n\n\n<li>It is used to create cyclic indole.<\/li>\n\n\n\n<li>It also played a role in the synthesis of five-membered pyrroles.<\/li>\n\n\n\n<li>A Dieckmann cyclization&#8217;s cyclic beta-keto ester product can be changed using reactions similar to those utilized in acetoacetic ester synthesis.<\/li>\n\n\n\n<li>The beta-keto ester&#8217;s acidic alpha-hydrogens allow it to be easily deprotonated and alkylated in an alpha-substitution process. The presence of a carbonyl group in the beta position enables the ester to be removed via decarboxylation. As a result, this procedure can be used to&nbsp;prepare 2-substituted cyclopentanones and cyclohexanones.<\/li>\n<\/ul>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"limitations-of-dieckmann-condensation\"><\/span><strong>Limitations of Dieckmann condensation<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>Esters of dibasic acids with fewer carbon atoms cannot proceed through Dieckmann condensation due to the high strain generated in the tiny rings.<\/li>\n\n\n\n<li>Esters of dibasic acids with more than eight carbon atoms do not undergo the Dieckmann reaction because the intramolecular reaction slows down as the chain length grows and the&nbsp;intermolecular condensation process is preferred.<strong><\/strong><\/li>\n<\/ul>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"-references\"><\/span><strong>&nbsp;<\/strong><strong>References<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>Morrison R. T. &amp; Boyd R. N. (1983).&nbsp;<em>Organic chemistry<\/em>&nbsp;(4th ed.). Allyn and Bacon.<\/li>\n\n\n\n<li>Smith M. &amp; March J. (2001).&nbsp;<em>March\u2019s Advanced Organic Chemistry: Reactions Mechanisms and Structure<\/em>&nbsp;(5th ed.). Wiley.<\/li>\n\n\n\n<li>Ghosh, S.K.,&nbsp;<em>Advanced General Organic Chemistry<\/em>, Second Edition, New Central Book Agency Pvt. Ltd., Kolkatta, 2007.<\/li>\n\n\n\n<li>Bahl, B.S., A., Advanced Organic Chemistry, S. Chand and Company Ltd, New Delhi, 1992. production of polyesters, polyurethanes, and alkaline resins.<\/li>\n<\/ul>\n","protected":false},"excerpt":{"rendered":"<p>Dieckmann condensation involves the intramolecular condensation of diester in the presence of&nbsp;bases to produce \u00df-keto esters.&nbsp;It is named after the German chemist Walter Dieckmann. The Dieckmann Condensation is effective for &#8230; <a title=\"Dieckmann Condensation: Mechanism, Applications, Limitations\" class=\"read-more\" href=\"https:\/\/thechemistrynotes.com\/dieckmann-condensation-mechanism-application\/\" aria-label=\"Read more about Dieckmann Condensation: Mechanism, Applications, Limitations\">Read more<\/a><\/p>\n","protected":false},"author":4,"featured_media":46895,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[21],"tags":[2780,2778,2781,2779],"_links":{"self":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/46891"}],"collection":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/comments?post=46891"}],"version-history":[{"count":2,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/46891\/revisions"}],"predecessor-version":[{"id":46896,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/46891\/revisions\/46896"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media\/46895"}],"wp:attachment":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media?parent=46891"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/categories?post=46891"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/tags?post=46891"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}